Hawaii Vacation Rentals – Island Condos, Beachfront Homes & Luxury Villas
Welcome to your guide for Hawaii vacation rentals, where tropical luxury meets everyday comfort. From sunrise-facing lanais on Maui to private bungalows near the lush valleys of Kauai, each rental is handpicked for quality, location, and local charm.
Why Book a Vacation Rental in Hawaii?
Unlike traditional hotels, vacation rentals provide full kitchens, private lanais, and dedicated living space—ideal for families, couples, or long stays. Many homes are steps from the beach, offer high-speed Wi-Fi, and include perks like pools, BBQ areas, or resort access.
Popular Vacation Rental Locations
- Waikiki, Oahu – High-rise condos near beaches, shops & nightlife
- Kihei, Maui – Walkable, affordable, and family-friendly
- Princeville, Kauai – Scenic cliffs, golf, and luxury condos
- Kailua-Kona, Big Island – Oceanfront escapes with sunset views
Rental Types Available
- Beachfront Condos with resort amenities
- Private Beach Homes with full kitchens
- Luxury Villas with pools & panoramic views
- Studios & Bungalows for solo travelers or couples
What Makes To-Hawaii.com Rentals Stand Out?
- Verified properties across all major Hawaiian islands
- Detailed descriptions, amenities, and photo galleries
- Helpful internal links to top Hawaii activities and Hawaii rental cars
- Flexible booking options, from weekend getaways to long-term stays
Plan Your Dream Island Escape
Explore the beauty of the islands with confidence. Whether you're whale watching on Maui, snorkeling on Oahu, or enjoying a peaceful sunrise on Lanai, our vacation rentals offer the perfect base for unforgettable memories. Start planning your Hawaiian adventure today.
Luxurious Oceanfront Escape Awaits – Stunning Views & Top-Floor Waikoloa Living!
Aloha and welcome to the idyllic gated community of Hali'i Kai! We're thrilled to introduce you to our exquisite, 180-degree oceanfront condo, where luxury meets affordability, and offers all the indulges, beauty, and relaxation that the Big Island has to offer....
Kona Acres Vacation Home
This vacation home is your destination if you desire privacy, have a family or want a laid-back vacation. This luxury home is ideal for large family gatherings. The house is located on a secluded one-acre, tropically landscaped lot in a quiet, quality Hawaii...
POIPU RESORT, 2BDRM, F/K, Washer/Dryer, POOL, WIFI, daily fresh towel exchanges
ALOHA! This 2 bedroom, 2 bathroom condo is located in the beautiful resort called "The Point at Poipu", a family friendly resort.Gorgeous 2 BEDROOM, 2 BATHROOM (King in master and 2 Twins or we can request a Queen for the 2nd bedroom), OCEANFRONT RESORT, short walk to...
Private KÅloa Retreat | Pool + Golf Course Views | Near PoÊ»ipÅ« Beach
Discover this lovely 3-bedroom gem in Kōloa. This awesome house features two king beds and two queen beds perfect for families or friends looking for a relaxing island retreat. With three full bathrooms including walk-in showers, a soaking tub in the master suite, and a...
Modern & Polished Oceanfront Vistas
Summary:Bright, modern, and spacious. Complete remodel in December 2021! Thoughtfully designed to elevate your experience with us. This one-bedroom, one-bathroom condo features luxurious touches throughout paired with beautiful ocean views. Located in the sunny and...
OCEAN VIEW STUNNER, SNORKEL w/ TURTLES, PRIVATE COVE
EPIC OCEAN VIEWS, close to restaurants and dining, family-friendly activities, public transport, and nightlife. You’ll love our place because of the neighborhood, comfy bed, coziness, views and the kitchen. Our home is good for couples or families.“Honokeana Cove has a...
Wailea Elua #2107 - Spacious, Stylish & Just Moments from Wailea Beach
Wailea Elua #2107 – Your Serene Wailea EscapeWelcome to Wailea Elua Village, a peaceful, terraced beachfront property located in the heart of the Wailea resort community. This low-density gated complex features two-story buildings set on 24 acres of lush tropical...
REMODELED Tropical Paradise 1BR unit in Princeville with AC & assigned parking!
Beautiful TOTALLY REMODELED 1 br/1 ba unit with living room, full kitchen washer/dryer and spacious lanai in heart of Princeville.ASSIGNED PARKING SPACE!Great views of Princeville golf course and mountains!Unit furnished with portable A/Cs in the bedroom and the living...
Kamaole Sands 7-405 - Stunning Renovation, Large Lanai, Ocean Views, Split AC!
Welcome to Kamaole Sands 7-405, your luxurious tropical escape in the heart of South Kihei, Maui! This stunning top-floor 2-bedroom, 2-bathroom condo is the ultimate destination for an unforgettable island getaway. With breathtaking views of the lush tropical courtyard...
Cozy 2-bedroom apartment in Honolulu
Consider this apartment your home away from home while you visit Honolulu. With 2 bedrooms featuring a queen and king bed, this cool space is perfect for guests looking for a comfortable stay. Fall in love with Honolulu and enjoy the magic it has to offer.
Amazing Views, Walking Distance to Beaches - Kapalua Bay Villa #14B1 - Quam Properties
Kapalua Bay Villa 14B1 is a one-bedroom condo featuring amenities such as picturesque ocean views, vibrant tropical decor, and complimentary high-speed wireless internet. The condo can accommodate up to four guests with a Cal King bed in the bedroom, a small private...
NEW! Beachfront, Amazing Views, AC, Hear the Ocean, Beautiful Spacious Remodel
Welcome to our oceanfront condo, Beachfront in Maui! Whether you are planning a romantic getaway for two or a family vacation, you will find everything you need at this PRIME location beachfront in Maui!**NEW - Captain Jack's Island Grill Restaurant just opened January...
Breathtaking Ocean Views from 3rd Row Luxury Villa at Ho'olei
Come relax and enjoy your stay at our spectacular ocean-view luxury villa, located directly across from the Grand Wailea Hotel & Spa on the beautiful island of Maui.Situated on the third row at Ho'olei, this beautiful two-story villa boasts dramatic Pacific Ocean views...
Ocean Views W/Lanai, WiFi, Cable, Fans–KIA #2179
Recently remodeled and redecorated, this bright and breezy 'home away from home' will make you want to return each year. This 880 square foot space is accentuated with a variety of darker woodish tones featured in the modern rattan furniture to the reddish flooring...
1 Acre PRIVATE RESORT,4 bed, 3 bath, cinema, spa
Summary:Rated in top 10 Airbnb's on the coast. Treat yourself to a vacation surrounded by unmatched landscaping, ocean view, 2000 sq/ft single level, fully stocked home with 4 bedroom, 3 bathrooms, Movie Theater; a/c in each room, waterfall, grotto, tiki torches, fruit...
🏖️Ocean Front - Direct View of Kailua Bay | Concierge Included | Nicely Renovated
vrKCV - Alii Villas 329, Professionally Managed by Kona Coast VacationsWelcome to Your Kona Home Away from Home at Alii Villas!Discover the perfect island escape for families or couples seeking relaxation, adventure, and unforgettable sunsets. This beautifully upgraded...
Spectacular Oceanfront 3 BR Home - Privacy & Space with Incredible Views!
Kealia Landing sits on a bluff overlooking wide, sandy Kealia Beach with panoramic, unforgettable views of Kauai's east coast extending ten miles to the Hoary Head Mountain range. From this wonderful cul-de-sac in an historic mill community, recreational possibilities...
Exquisite Luxury: Oceanview Penthouse Villa
Beautiful second home of kama'aina family right next to Mauna Lani's white sand beaches with access to a pool, spa, and grill area that face the ocean. This one bedroom penthouse villa, K302, provides utmost privacy and beauty with spectacular pond, ocean, and sunset...
Hale Kalea – Renovated 4BR Luxury Home at Mauna Lani with Pool, Views & Golf Cart
Welcome to Hale Kalea, the House of Joy and Happiness! After many years as a successful vacation rental, Hale Kalea has new owners and we can’t wait to welcome you back!Located in the Mauna Lani Resort’s exclusive gated community of Champion Ridge and perched above the...
NEWLY REMODELED! Partial Ocean View condo along the golf course
This newly remodeled 3 bedroom 2 bath condo located in the heart of Wailea is the perfect vacation oasis for your island getaway. This condo comfortably sleeps 6 and has amenities such as 2 outdoor pools each with a hot tub, a full kitchen, wireless internet, air...
Lae Nani 531-Oceanfront View Top Floor with AC
Welcome to Lae Nani Oceanfront Penthouse Unit 531, where paradise awaits! This exquisite two-bedroom, two-bathroom condo promises an unforgettable vacation experience in the heart of Kauai's Coconut Coast. As you step into this Royal Hawaiian-inspired penthouse, you'll...
WHALE'S TAIL -Beachfront in Magical Puako! Ocean playground outside the door!
Combine the sandy beach next to your back yard with the thoughtfully placed windows that give you excellent views from nearly every spot in the house—upstairs and down—and you’ll love the Whale’s Tail for your Hawaii vacation. Not only is the entire ocean-facing wall...
Nihi Kai 802 Sunset Spectacular, Ocean Views, w/AC
Summary:Enjoy spectacular sunsets and sweeping ocean views at Nihi Kai 802, a beautifully remodeled 2BR/2BA condo with full A/C. Located just a short walk to Poipu Beach and Brennecke’s Beach, this spacious retreat features an upgraded kitchen, modern bathrooms,...
The Catbird Seat -Closest Vacation Home To Poipu Beach - 100 Ft Away!!! Pool!!
The Catbird Seat private paradise home is the closest location to Poipu Beach and Brennecke Beach of ANY vacation rental. 2 Bedrooms sleep 4. Your choice of twin beds or a King in the 2nd bedroom.This ideal spot is just across from the world famous Brennecke Beach and...
Enjoy Maui Sunsets from Kapalua Golf Villa 15T2
Experience Golf Course Luxury at Kapalua Golf Villa 15T2Welcome to Kapalua Golf Villa 15T2—your private retreat in one of Maui's most prestigious resort communities. This beautifully upgraded 1-bedroom, 1.5-bathroom townhome offers sweeping views of the Bay Course and...
Beautiful Newly Remodeled Condo in Kahana, Maui
Beautiful, newly remodeled one bedroom condo that sleeps four in Kahana, Maui. Situated in Keoni Nui bay with magnificent views of Lanai, just steps from a beautiful pool and beach just for the condominium complex. The condo (#C3C) features a large kitchen, California...
Hale Ka Mahina, walk to Hanalei Bay & town. TVNC-1115
Upgraded in 2019, Hale Ka Mahina isn't your average vacation rental, Hale Ka Mahina is tucked away on a side street between Hanalei Bay and Hanalei town. Easily walk or ride bikes to the beach and town when you want to check the surf or grab a coffee at the Hanalei...
Colorful & open condo w/free WiFi, furnished deck, & shared pool - near golf
Mauna Kai 6BOur calendar is updated in real-time & our nightly rates are accurately displayed. Simply enter your desired dates and click 'Book Now!'Enjoy a taste of the tropics inside this open, colorful, and very inviting condo located near golf courses, beaches, and...
Gorgeous studio apartment on the Hamakua Coast 6 minutes to downtown Hilo. 99/nt
Nicely furnished, recently remodeled large (5-600 SF) Studio unit on a beautiful gorge with nearby waterfall and swimming pond. Unit has own kitchen, full private bath, shared yard, laundry, outdoor shower, sauna & hot tub. Also has cable TV & Wi-Fi and private...
Penthouse Sweeping Ocean Views!
Welcome to Maui and the Hono Hideaway home located in the stunning Ka`anapali Shores Resort!See the ocean from every room of this beautiful, top-floor FOUR-story condo in the oceanfront wing of the Ka`anapali Shores resort! You`ll feel like you`re walking on water as...
Maui is calling....it's a great time to take a trip!
You will really enjoy our condo, wake up and fall asleep to the lull of ocean sounds. View the water from almost every part of the condo. There is a clean and well equipped kitchen with full size range and refrigerator for your convenience. An outdoor BBQ grilling area...
Luxury Penthouse at Beach Villas at Ko Olina
This penthouse villa has 3 bedrooms and 3 baths and is located on the top/4th floor in the Ocean Tower (O426). The villa has an unobstructed full front ocean view and the private lanai overlooks the peaceful and tranquil koi pond area of the resort. Open the large glass...
Just a couple houses away from the nicest beach on the island.
This rental is across the street from one of the nicest beaches on the island. Don't take our word for it check out the pictures of Waimanalo Beach and Bellows Beach. Kitchen has everything you need and opens up to a dinning table to enjoy your meals or you can take...
Ko Olina Beach Villas B506 by Gather: Luxury 2BD 2BTH w/ Ocean Views
Ko Olina Beach Villas B506 by Gather offers an elevated blend of comfort, elegance, and breathtaking ocean scenery from its desirable fifth-floor position in the Beach Tower. This beautifully appointed two-bedroom, two-bath villa accommodates up to six guests, making it...
Comfortable Hawaiian Style Home
This cozy and comfortable Hawaiian style redwood home is just a short walk to miles of sandy beach. The house is surrounded by lush, tropical gardens. Two lanais let you enjoy paradise in comfort and privacy. A wonderful place to get away and relax in quiet and comfort....
New Listing- Spacious, Remodeled Direct Beachfront with A/C & on Sandy Beach
Our condo is zoned "Hotel/Resort" so no need to worry about our zoning.Hear the Waves....Lay in bed and listen to the waves! Spacious condo with direct beach & ocean view. A Sandy Swimmable beach is right outside your door. *** Book with confidence! You will be offered...
Maui Resort Rentals: Honua Kai Konea 406 - Extra Large One Bedroom Den, Partial Ocean and West Maui Mountain Views!
Konea 406 is an expansive one-bedroom suite boasting views of what West Maui is most famous for, the blue Pacific Ocean and the lush West Maui Mountains.An additional den area offers fantastic value unique to this class of suites at Honua Kai.When it's time to rest, the...
Wai Lani: Ocean View Home, AC & Lanais
Wai Lani by Gather offers an elevated Princeville escape where breathtaking ocean views, cooling trade winds, and thoughtful modern comforts come together in perfect harmony. Perched at the end of Albert Road and surrounded by lush tropical beauty, this serene retreat...
KBM Resorts | FREE CAR | Kapalua Golf Villa | Ocean view | 1-Bedroom Condo, Recently Remodeled! KGV-20T8
** Limited Time Special Offer: Reserve any KBM Resorts property in Hawaii with an arrival date between now and December 31, 2026 for 6 nights or more and receive a FREE 4-door rental car from top providers--Hertz, Alamo, Avis, or Budget. Convenient airport pick-up and...
Location, Location, Beautiful AC Beach Studio In Hilo; Few Steps from Beach Cove
WHY STAY ANYWHERE IN HILO BUT CLOSE TO BEACHES AND OCEAN WHERE THE WEATHER IS BEST!!! Lovely beach studio located a minute walking distance to ocean with small swimming cove and tide pools. The studio is AC comfortable which ensures cool and comfortable days and...
Mesmerizing Oceanfront 2 Bedroom | 2 Bathroom with Central Air
Lanikai 134 – Mesmerizing Oceanfront Top-Floor Retreat with Central A/CWelcome to Lanikai 134, a spacious third-floor oceanfront condo offering breathtaking views of Wailua Bay and cool comfort with central A/C throughout. With two bedrooms, two bathrooms, and a...
🏖 ❤️ LARGE LUXURY GROUND FLOOR LUANA VILLA,POOL VIEWS, GRT LOCATION & Reviews❤️
🌺 You are renting directly from the owners. We would love to have you stay in our villa. Enjoy all the amenities that Honua Kai has to offer. 🌺 One of the closest Luana Villas to the ocean. 🌺 Over 40 great reviews! Please read what others are saying about our villa.🌺...
Walk to Pipeline Rocky Point and Waimea
Beachfront property on Northshore Oahu. Beautiful home on the beach with close access to numerous activities. Gated property with lots of privacy, beachside lanai and memorable sunsets. House has 3 Bedrooms and 2 full Bathrooms with ac in all rooms included. Covered...
Aloha Condos, Kanaloa at Kona, Condo 2204, Oceanfront, AC
Kanaloa at Kona Condo 2204 is a dream! With breathtaking ocean views and luxurious amenities, this condo exceeds expectations. Guests love the well-appointed kitchen, comfy furnishings, and thoughtful extras like beach gear and toiletries. The lanai is perfect for...
Lae Nani 512 Gorgeous Ocean Front Ground Floor in Building Five With AC
Lae Nani is a premier property on the Coconut Coast centrally located near grocery stores, galleries, restaurants, small boutique shops, etc.Our condo is on the ground floor in Building Five and here are some of the features:-Location Location Location-Air Conditioning...
Majestic Mahakea – Oceanfront Oasis on Oahu's North Shore
Majestic Mahakea Oceanfront Oasis invites you to experience beachfront luxury on Oahu’s fabled North Shore. This modern two-story residence sits directly on Mahakea Beach, where turquoise waves meet a lush mountain backdrop. Designed for both serenity and connection,...
Makena Surf F306 Beachfront Resort - 2 Bedroom Oceanfront Condo
Experience effortless mingling and entertaining in Makena Surf F306, where the open living area seamlessly connects to a spacious lanai. Enjoy the refreshing ocean breezes beneath the cathedral ceilings while taking in the stunning ocean views. This residence boasts...
⭐️ NEW KITCHEN - Large lanai with best views of sunsets, pool & grounds ⭐️
Spectacular, nicely decorated, across the street from Kamaole Beach III in Kihei!Feast your eyes on this fabulous condo with a lanai to die for.Enjoy this spacious and tastefully furnished 818 sq. ft. condo with views of the pool, tropical gardens and sunsets. The unit...
KBV 15B2 2BD Kapalua Breathtaking Panoramic Ocean views
Kapalua Bay Villas 15B2 NEW LISTING! Breathtaking 2 Bedroom, 3 Bathroom with Panoramic Ocean views in the heart of Kapalua FREE daily activities included with your stay value up to $1035! Complimentary admission, every day of your stay*: Lu'au, Golf, Whale Watch...
2Bed/1Bath Upstairs Home, 1mile to Beach, Next to State Forest, Custom Finishes
There is a black sand beach nearby to explore (Kehena), and a lava tube hidden in a kipuka surrounded by a lava field, and geothermally heated ponds, forest trails, farmers’ markets, yoga classes, chocolate and mushroom farms, dances, waterfalls, drum circles and maybe...